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123-62-6Relevant articles and documents
Diastereoselective synthesis of a lilac aldehyde isomer and its electrophysiological detection by a moth
Schneider, Marc-Andre,Doetterl, Stefan,Seifert, Karlheinz
, p. 1252 - 1259 (2013)
The monoterpene lilac aldehyde (=2-(5-ethenyl-5-methyloxolan-2-yl)propanal) is a widespread flower scent. Lilac aldehyde is emitted in high amounts from nocturnal plant species, and it is highly attractive to nocturnal moth pollinators, such as Hadena bicruris, the pollinating seed predator of Silene latifolia. Lilac aldehyde possesses three stereogenic centers and can occur in eight stereoisomers which induce different antennal responses in H. bicruris. The distribution pattern of stereoisomers differs among plant species, and if H. bicruris has different receptors for detecting different isomers, it may use these differences to discriminate flowers of S. latifolia hosts from flowers of non-host plants. To investigate the question whether the moths have in their antennae one olfactory receptor or several different receptors for the detection of the single lilac aldehyde isomers, (2S,2′S,5′S)-lilac aldehyde was diastereoselectively synthesized. (2S,2′S,5′S)-Lilac aldehyde and its isomeric mixture were tested electrophysiologically on antennae of H. bicruris. The results displayed antennal responses, which are characteristic for a single receptor that detects the different lilac aldehyde isomers. Copyright
A facile method for Rh-catalyzed decarbonylativeortho-C-H alkylation of (hetero)arenes with alkyl carboxylic acids
Tian, Yiqiang,Liu, Xiaojie,He, Bangyue,Ren, Yuxi,Su, Weiping
, p. 19827 - 19831 (2021)
A facile and effective method for Rh-catalyzed directortho-alkylation of C-H bonds in (hetero)arenes with commercially available carboxylic acids has been developed. This strategy was initiated byin situconversion of carboxylic acids to anhydrides which, without isolation, underwent Rh-catalyzed direct decarbonylative cross-coupling of aryl carboxamides containing 8-aminoquinoline. The reaction proceeds with high regioselectivity and exhibits a broad substrate scope as well as functional group tolerance.
Generation of basic centers in high-silica zeolites and their application in gas-phase upgrading of bio-oil
Keller, Tobias C.,Rodrigues, Elodie G.,Perez-Ramirez, Javier
, p. 1729 - 1738 (2014)
High-silica zeolites have been reported recently as efficient catalysts for liquid- and gas-phase condensation reactions because of the presence of a complementary source of basicity compared to Al-rich basic zeolites. Herein, we describe the controlled generation of these active sites on silica-rich FAU, BEA, and MFI zeolites. Through the application of a mild base treatment in aqueous Na2CO3, alkali-metal-coordinating defects are generated within the zeolite whereas the porous properties are fully preserved. The resulting catalysts were applied in the gas-phase condensation of propanal at 673 K as a model reaction for the catalytic upgrading of pyrolysis oil, for which an up to 20-fold increased activity compared to the unmodified zeolites was attained. The moderate basicity of these new sites leads to a coke resistance superior to traditional base catalysts such as CsX and MgO, and comparable activity and excellent selectivity is achieved for the condensation pathways. Through strategic acid and base treatments and the use of magic-angle spinning NMR spectroscopy, the nature of the active sites was investigated, which supports the theory of siloxy sites as basic centers. This contribution represents a key step in the understanding and design of high-silica base catalysts for the intermediate deoxygenation of crude bio-oil prior to the hydrotreating step for the production of second-generation biofuels. Creating new basic sites: Through activation treatments in alkaline media, basic sites with high activity, stability, and selectivity are generated in high-silica FAU, BEA, and MFI zeolites, which enable the efficient deoxygenation of pyrolysis oil by condensation reactions. Intermediate bio-oil upgrading is key for the sustainable and profitable production of advanced biofuels.
Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides
Ong, Jun-Yang,Ng, Xiao Qian,Lu, Shenci,Zhao, Yu
supporting information, p. 6447 - 6451 (2020/09/02)
We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, (S)-HBTM, with a simple procedure. The N-sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone.
Metal-free oxidative self-coupling of aldehydes or alcohols to symmetric carboxylic anhydrides
Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 2533 - 2536 (2017/06/13)
A metal-free synthesis of symmetrical anhydrides has been developed starting from aldehydes, both aliphatic and aromatic or primary benzylic alcohols. The reaction occurs at room temperature and makes use of trichloroisocyanuric acid (TCCA) as an oxidant providing the desired carboxylic anhydrides in satisfactory yields.
Anhydrides from aldehydes or alcohols via oxidative cross-coupling
Gaspa, Silvia,Amura, Ida,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 931 - 939 (2017/02/10)
A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.
An anhydride producing method
-
Paragraph 0035; 0036, (2017/06/24)
An anhydride producing method is disclosed. The method includes oxidizing a C2-C7 alcohol or a C2-C7 aldehyde under the existence of a catalyst and an oxidant to obtain an anhydride, wherein the reaction pressure is atmospheric pressure, the temperature is 50-200 DEG C, the hourly space velocity is 0.5-100 h, the catalyst is a supported type Pd catalyst and the oxidant is oxygen or air. The method adopts the oxygen as the oxidant, and achieves high-selectivity conversion of the alcohol or the aldehyde to the anhydride through an oxidizing manner. Anhydride selectivity is 10-85%. A substrate conversion rate is 10-100%. The yield of the anhydride is 10-85%. The method does not need a high reaction temperature and can be performed at room temperature or a temperature close to room temperature, thus saving a large amount of energy. The method is low in equipment requirement, low in investment, simple in reaction system and easy in industrialization. The catalyst is long in service lifetime and free of loss.
Alcohol cross-coupling for the kinetic resolution of diols via oxidative esterification
Hofmann, Christine,Schümann, Jan M.,Schreiner, Peter R.
supporting information, p. 1972 - 1978 (2015/02/19)
We present an organocatalytic C-O-bond cross-coupling strategy to kinetically resolve racemic diols with aromatic and aliphatic alcohols, yielding enantioenriched esters. This one-pot protocol utilizes an oligopeptide multicatalyst, m-CPBA as the oxidant, and N,N-diisopropylcarbodiimide as the activating agent. Racemic acyclic diols as well as trans-cycloalkane-1,2-diols were kinetically resolved, achieving high selectivities and good yields for the products and recovered diols.
Kinetic analysis of the HBTM-catalyzed esterification of an enantiopure secondary alcohol
Wagner, Alexander J.,Rychnovsky, Scott D.
supporting information, p. 5504 - 5507 (2013/11/19)
A detailed kinetic analysis of the homobenzotetramisole-mediated esterification of the enantiopure secondary alcohol (1R,2S)-2-phenylcyclohexanol is presented. The results of this analysis show that the reaction is first order in the homobenzotetramisole catalyst, first order in (1R,2S)-2- phenylcyclohexanol, and first order in propionic anhydride. Initial rates, the turnover frequency of the catalyst, and different excess plots were utilized in this evaluation. Additionally, a same excess plot revealed no noticeable catalyst decomposition or product inhibition during the course of the reaction.
Ruthenium-catalyzed transvinylation - New insights
Ziriakus, Jennifer,Zimmermann, Teresa K.,P?thig, Alexander,Drees, Markus,Haslinger, Stefan,Jantke, Dominik,Kühn, Fritz E.
, p. 2845 - 2859 (2014/03/21)
The use of ruthenium complexes in transvinylation catalysis has been well established since the 1980s. However, the reaction mechanism and the active catalyst species, which is presumed to contain ruthenium carbonyl carboxylate entities, have so far remained elusive. In this work the synthesis and characterization of three novel ruthenium complexes comprising ruthenium carbonyl carboxylate structural motifs including two single crystal structures as well as the crystal structures of two known ruthenium complexes are reported. These new complexes and four known ruthenium complexes with appropriate structural motifs were applied in transvinylation catalysis. Mechanistic studies including identification and characterization of the active species, isotope labeling experiments and examination of the regioand stereoselectivity of the transvinylation reaction are presented, resulting in the proposal of a probable reaction mechanism, which is supported by DFT calculations on the B3LYP/6-31G* level of theory.